Synthesis of (S)- and (R)-tert leucine enabling direct coupling with α-amino acid esters via β-lactam-derived α-amino acid N-carboxy anhydrides

Tetrahedron Letters

Volumn 38, Issue 17, 1997, Pages 3093-3096

  Palomo, Claudio ^a   Ganboa, Iñaki ^a   Odriozola, Beatriz ^a   Linden, Anthony ^b  

^a UNIVERSITY OF THE BASQUE COUNTRY UPV EHU   (Spain)

^b UNIVERSITY OF ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID SYNTHESIS; ARTICLE; CHIRALITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030890690     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00553-4     Document Type: Article

References (15)

1. For a recent review, see: Bommarius, A.S.; Schwarm, M.; Stingl, K.; Kottenhahn, M.; Huthmacher, K.; Drauz, K. Tetrahedron: Asymmetry 1995, 6, 2851.
2. a) Freskos, J.N. Synthetic Commun. 1994, 24, 557.
3. b) Turner, N.J.; Winterman, J.R.; McCague, R.; Parratt, J.S.; Taylor, S.J.C. Tetrahedron Lett. 1995, 36, 1113.
4. c) Drauz, K.; Jahn, W.; Schwarm, M. Chem. Eur. J. 1995, 1, 538.
5. Palomo, C.; Aizpurua, J.M.; Cuevas, C.; Urchegui, R.; Linden, A. J. Org. Chem. 1996, 61, 4400.
6. a) Rogalska, E.; Belzecki, C. J. Org. Chem. 1984, 49, 1397.
7. b) Georg, G.I.; Wu, Z. Tetrahedron Lett. 1994, 35, 381.
8. For a solution to this problem by using racemic α-(2,6-dichlorophenyl)ethyl amine, see: c) Hashimoto, Y; Kai, A.; Saigo, K. Tetrahedron Lett 1995, 36, 8821.
9. Thomas, R.C. Tetrahedron Lett. 1989, 30, 5239.
10. Aszodi, J.; Bonnet, A.; Teutsch, G. Tetrahedron 1990, 46, 1579.
11. 3H).
12. 4 position in 2b shows as a doublet at 3.41 ppm, while the corresponding one in 3b appears at 3.58 ppm.
13. Preparative HPLC was performed on a Lichrosorβ-Si60 7μM column with flow rates of 10 ml/min. (EtOAc/Hex., 40:60) and using a UV detector (254 nm). Retention times: 4, 32.55 min. and 5, 38.74 min.
14. The X-ray data have been deposited at Cambridged Crystallographic Data Center.
15. 25= +0.7 (c=0.7, MeOH).